Methylamine → (Z)-4-hydroxy-N-methyl-3-(pyridin-4-yl)-2-(4-(quinolin-2-ylmethoxy)phenyl)but-2-enamide

HRID 1258237Notes

Reaction equation

HRID 1258237 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH2:11][O:10][C:9](=[O:12])[C:8]=2[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=3)=[CH:15][CH:14]=2)=[CH:3][CH:2]=1.[CH3:31][NH2:32]>CO>[OH:10][CH2:11]/[C:7](/[C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1)=[C:8](/[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=2)=[CH:15][CH:14]=1)\[C:9]([NH:32][CH3:31])=[O:12]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 44537962HCID 44537962, compound

Product 1

HCID 59354792(Z)-4-hydroxy-N-methyl-3-(pyridin-4-yl)-2-(4-(quinolin-2-ylmethoxy)phenyl)but-2-enamideYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(pyridin-4-yl)-3-(4-(quinolin-2-ylmethoxy)phenyl)furan-2(5H)-one (1.0 g, 0.002 mol) and MeNH2 in MeOH (25 mL) was refluxed for 1 h. The reaction mixture was concentrated in vacuo to afford (Z)-4-hydroxy-N-methyl-3-(pyridin-4-yl)-2-(4-(quinolin-2-ylmethoxy)-phenyl) but-2-enamide (920 mg, 86%) as a solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-4dd7e21652224c2ab3cd5df7e87955f3
Source dataset
uspto-grants-2013_06
Patent number
US08466148B2

Reaction notes

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